Sideshow Bob was released by Democratic mayor Joe Quimby after pressure from Republican-inspired protests. In "Black Widower" he claimed he and his prisonmates would be released on the streets once the Democrats were back in power.

Some prints of this episode cut the whole intro, as the text reveals the TV credits.

Fox Broadcasting Company said that the episode was running too long to have the couch gag. Along with "Bart The General" And "Life on the Fast Lane," the episode Marks this one as the third episode to not have a couch gag or any gags.

The Springfield Republican party members are:

Rich Texan

Dracula

Birchibald T. Barlow

Rainier Wolfcastle

Blue Haired Lawyer

Dr. Hibbert.

Sideshow Bob's middle name "Underdunk" is mentioned for the first time.

The end of the episode, where the prison rowing team is going to compete against Princeton alumni, is the first time Bob is disparaging towards the school (the second is when he refers to it as "clown college" in Brother from Another Series).

In the Mythbusters "The Simpsons Special" episode, Adam and Jamie tested a myth about this episode: A person hanging onto a wrecking ballcan protect a house from damage if the ball swings to pin him against the wall? to test this myth, they built a real life Homer Simpson with rubber and filled with water to match Homer's weight (239 pounds). in the final test, Homer was intact, but the house was damaged. The myth was classified as "Plausible".

This is the first time in the series were the catchphrase "Meh" is used, with a Librarian using it to answer Lisa's interjection about votes being secrets.

Though never explicitly stated, the reason Smithers helps the kids to take down Sideshow Bob in secret by giving them information is likely due to the fact that Bob is affiliated with the Republican Party, who have a long tradition of being opposed to gay marriage; something that would not sit well with the closeted Smithers.

Only names of dead people and animals appear on the voter records, but Bart's elephant Stampy, one of voters, is not dead or buried at the Springfield Pet Cemetery. It never said it was only dead animals, since animals are unable to vote, Bob only put as many names as possible.

The title is a reference to the film Bob Roberts, a 1992 film following the eponymous politician, suggesting that success comes from shady deals, hypocrisy and deceit. Bob enters the meeting wrapped in an American flag, a reference to the film's poster.

Archie, Jughead and Reggie from the Archie Comics throw Homer out of their car, while Moose says, "Duh, stay out of Riverdale!" It is not known how he met them or what he did to offend them (and presumably the community they lived in).

Homer later refers to them again; he is seen reading an Archies comic and comments, "Riverdale punks, think they're too good for me!"

In court, Bob says, "You want the truth? You can't handle the truth!" A reference to a line from the movie A Few Good Men starring Jack Nicholson.